Flexible enantiodivergent synthesis and biological activity of mannostatin analogues, new cyclitol glycosidase inhibitors

被引：23
|
作者：
Nishimura, Y
Umezawa, Y
Adachi, H
Kondo, S
Takeuchi, T
机构：
[1] Institute of Microbial Chemistry, Shinagawa-ku, Tokyo 141
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期
关键词：
D O I：
10.1021/jo951126v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mannostatin A (1) is a new cyclitol inhibitor of glycoprotein processing. 2-Epimannostatin A (12) and its enantiomer (13) as well as their positional isomers (14, 15) were designed for probing structure-activity relationships in this class of glycosidase inhibitors. The analogues have been synthesized from (S)-4-((tert-butyldimethylsilyl)oxy)-2-cyclopentenone by an enantiodivergent strategy in a totally stereospecific fashion. Compound 13 showed inhibition against almond P-glucosidase and is shown to be a topographical analogue of beta-D-glucopyranoside.
引用
收藏
页码：480 / 488
页数：9
相关论文
共 50 条
  • [21] Synthesis and glycosidase inhibitory activities of chain-modified analogues of the glycosidase inhibitors salacinol and blintol
    Nasi, Ravindranath
    Sim, Lyann
    Rose, David R.
    Pinto, B. Mario
    CARBOHYDRATE RESEARCH, 2007, 342 (12-13) : 1888 - 1894
  • [22] Straightforward chemo-enzymatic synthesis of new aminocyclitols, analogues of valiolamine and their evaluation as glycosidase inhibitors
    El Blidi, Lahssen
    Ahbala, Mustapha
    Bolte, Jean
    Lemaire, Marielle
    TETRAHEDRON-ASYMMETRY, 2006, 17 (18) : 2684 - 2688
  • [23] Synthesis and biological evaluation of α-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A
    Ogawa, S
    Morikawa, T
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (11) : 1499 - 1504
  • [24] Polycyclitols: synthesis of novel carbasugar and conduritol analogues as potential glycosidase inhibitors
    Mehta, G
    Ramesh, SS
    TETRAHEDRON LETTERS, 2001, 42 (10) : 1987 - 1990
  • [25] Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors
    García-Moreno, MI
    Benito, JM
    Mellet, CO
    Fernández, JMG
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23): : 7604 - 7614
  • [26] Stereoselective synthesis of aminocyclopentitols as new glycosidase inhibitors
    Li, Qing Ri
    Dong, Guang Ri
    Kim, In Su
    Jung, Young Hoon
    DRUGS OF THE FUTURE, 2007, 32 : 68 - 68
  • [27] Synthesis of O-linked Cyclitol Analogues of Gilvocarcin M and Antibacterial Activity
    Sharif, Ehesan U.
    Shi, Pei
    O'Doherty, George A.
    ISRAEL JOURNAL OF CHEMISTRY, 2021, 61 (7-8) : 394 - 400
  • [28] Hemi-synthesis and biological activity of new analogues of podophyllotoxin
    Roulland, E
    Magiatis, P
    Arimondo, P
    Bertounesque, E
    Monneret, C
    BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) : 3463 - 3471
  • [29] Opioid peptides: Synthesis and biological activity of new endomorphin analogues
    Biondi, Barbara
    Giannini, Elisa
    Negri, Lucia
    Melchiorri, Pietro
    Lattanzi, Roberta
    Rosso, Federica
    Ciocca, Luigi
    Rocchi, Raniero
    INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2006, 12 (02) : 145 - 151
  • [30] Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues
    Kim, YB
    Kim, YH
    Park, JY
    Kim, SK
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) : 541 - 544
12345